High-yielding synthesis of Weinreb amides via homogeneous catalytic carbonylation of iodoalkenes and iodoarenes

Attila Takács, Andrea Petz, László Kollár

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Iodoarenes (iodobenzene and 2-iodothiophene) and iodoalkenes (1-iodocyclohexene, 1-iodo-4-tert-butylcyclohexene, 1-iodo-2-methylcyclohexene and 1-iodo-1-(1-naphthyl)ethene) were used as substrates in palladium-catalysed aminocarbonylation with N,O-dimethylhydroxylamine. The corresponding Weinreb amides were prepared in high isolated yields (up to 87%) when forcing conditions (40-60 bar of CO, 50 °C) were used. The aminocarbonylation provides the Weinreb amides as pure products in a chemoselective reaction. No formation of ketocarboxamides, due to double CO insertion, except for 2-iodothiophene, was observed even at 60 bar of CO pressure.

Original languageEnglish
Pages (from-to)4479-4483
Number of pages5
JournalTetrahedron
Volume66
Issue number25
DOIs
Publication statusPublished - Jun 19 2010

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Keywords

  • Aminocarbonylation
  • Carbon monoxide
  • Iodoalkene
  • Palladium
  • Weinreb amide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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